Chestertown is in Maryland's Eastern Shore.
Chestertown, the county seat of Kent, the Eastern Shore of Marylands's oldest county, was founded in 1706 and served as a port of entry during colonial times. A town rich in history, its attractions include a blend of past and present. Its brick sidewalks and attractive antique stores, restaurants and inns beckon visitors and residents alike to wander through the historic district and enjoy homes and places with architecture ranging from the Georgian mansions of wealthy colonial merchants to the elaborate style of the Victorian era.
Chestertown is situated on a scenic peninsula where the Chester and Sassafras rivers meander into Chesapeake Bay.
- Historic District - The best way to get around Downtown Chestertown is on foot. Everything you need to see is within walking distance and it's nice to stroll the brick sidewalks to see the sights. The main shopping area is on High Street and Cross Street, and the beautiful historic houses lining the water are just two blocks from the main strip of boutiques and restaurants.
- Washington College - The college is a very short drive away from the downtown area. Once there, it is easy to walk around the pretty campus and take the same steps that George Washington once did over 300 years ago.
- Chestertown Farmers' Market, located in Fountain Park on Park Row in the heart of downtown Chestertown at 118N Cross Street. It is open every Saturday morning, 8 am to noon, from the first Saturday in April until the last Saturday before Christmas. The market includes a variety of produce as well as meats, cheeses, soaps and lotions, and baked goods.
- Washington College, located in Chestertown. Washington College is a private liberal arts college that has roughly 51% in state students and 49% out of state students. The college was founded in 1782 and is the tenth oldest college in the United States.
- First Friday - The first Friday of each month, many stores in the downtown area participate in what is known as "First Friday". Participating stores and galleries extend their hours for gallery viewing and shopping. Usually from 5 pm until 8 pm.
- Galleries - Chestertown has many galleries and studios in its downtown area. The galleries features local and international artists.
- Chester River, easily accessed by going all the way down High Street, passing the Imperial Hotel on the left. There are benches and a park overlooking the river. Kayaks can be rented at certain locations along the river.
- Weekend Events - There are major weekend events in Chestertown. Such weekend events include the Wild Fowl Festival, Tea Party, Downrigging, and the Tall Ship Festival along the Chester River.
Located on Cross Street across the street from Play it Again Sam's coffee shop, Twigs and Teacups is a novelty store with unique gifts for all ages. Within the store are a wide variety of books on subjects such as cuisine, comic joke books, quotes and blank decorative notebooks. There is a clothing section in back for casual and earthy outfits and scarves. Also featured is a bath and body section for relaxation and gifting. The children's area has games, books, toys and crafts for many ages. Free gift wrapping is available on request. While you're there, try to find the store cat- often found sleeping within the many nooks- and always happy to have his head scratched.
For the more refined Chestertown gift shopper, Cornucopia of Gifts has a wide array of household decorative items, potpourri, candles, CD's, handbags and jewelry. Located on the opposite side of Cross Street from Twigs and Teacups, this store features an extensive back room with children's clothing and gifts- ideal for showers, grandchildren, nieces and nephews.
- The Front Room at the Imperial Hotel, . One of the most popular and high-end restaurants in town. Many locals and tourists find it to have the best food in Chestertown. There is an extensive wine list and the menu is filled with a variety of different choices, using fresh, regional ingredients. The restaurant offers seating outside during the Spring, Summer, and Fall seasons in the courtyard.
Play it Again Sam's (108 South Cross St) is the towns only coffee shop offering fresh brewed coffee, tea, pastries and some hand selected wine for sale by the bottle. You're likely to be in line next to some Washington College students and professors or the regulars around town. Many out of towners consider this a near perfect coffee shop!
- Andys - Lounge-style bar. Individuals must be 21 years or older to enter. It is a non-smoking restaurant and bar that offers music as well as weekly specials such as "tapas Tuesday" and "meatloaf Monday". The food menu and drink menu change seasonally.
- Great Oak Manor 10568 Cliff Road, Tel (800) 504-3098.  This bed and breakfast is ideal for secluded getaways to the Chesapeake Bay area. Far from any highway or large towns, our inn will relax you with the sounds of nature, the aura of yesteryear, and the comforts of modern society.
- The Imperial Hotel, 208 High Street, . Popular with the locals as well as tourists. Built in 1903, the Imperial Hotel has become a significant landmark in Chestertown and a must-see for many tourists. The Front Room Restaurant serves lunch and dinner Tuesday through Saturday and brunch on Sunday. The hotel has 11 rooms and 2 suites. Something unique about the Imperial Hotel is that each room has its own individual interior, furnished with authentic period furnishings and antiques.